Boron Trichloride → 2-Methyl-3-(4'-methoxycarbonyl-3'-hydroxyphenyl)-1-naphthol

HRID 5291

Reaction equation

[CH3:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[C:14]([O:22]C)[CH:13]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:24].B(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[C:14]([OH:22])[CH:13]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:24]

Participants

Conditions

Temperature: 25 °C

Procedure

To a cooled (-78° C.) suspension of 7.0 g of 2-methyl-3-(4'-methoxycarbonyl-3'-methoxyphenyl)-1-naphthol in 100 mL of methylene chloride was added, dropwise over 10 minutes, 26 mL of 1 M boron trichloride in methylene chloride. The resulting mixture was stirred overnight at 25° C. and then quenched with 25 mL of methanol. The solution was washed with 3×40 mL of 1 N hydrochloric acid and then 2×50 mL of saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residual oil was purified by flash chromatography (2:1 methylene chloride:hexane as eluent) to give 4.8 g of 2-methyl-3-(4'-methoxycarbonyl-3'-hydroxyphenyl)-1-naphthol as a white solid.

Workup

temperatureTo a cooled
additionwas added, dropwise over 10 minutes
customquenched with 25 mL of methanol
washThe solution was washed with 3×40 mL of 1 N hydrochloric acid
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residual oil was purified by flash chromatography (2:1 methylene chloride:hexane as eluent)

Sources & evidence

ORD record: ord-c12e9f988a1d48c99466fdb4537eb263
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244771

Linked notes

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